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Norwegian Joy
Norwegian Cruise Line
Feb 9, 2028 - Feb 18, 2028 (9 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Ocho Rios, Jamaica • Miami
Average Starting Price
$1,199pp
Jim's Onboard Credit
47% OFF
MSC Poesia
MSC Cruises
Oct 31, 2027 - Nov 11, 2027 (11 Nights)
Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami
Average Starting Price
$1,113pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,039pp
Jim's Onboard Credit
57% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jul 24, 2027 - Jul 31, 2027 (7 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami
Average Starting Price
$799pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$439pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 23, 2028 - Mar 15, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Nassau • Fort Lauderdale
Average Starting Price
$5,089pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Resilient Lady
Virgin Voyages
Mar 7, 2027 - Mar 13, 2027 (6 Nights)
Miami • Bimini • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$894pp
Jim's Onboard Credit
62% OFF
MSC Seashore
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocho Rios, Jamaica • George Town, Cayman Islands • Ocean Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$706pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

48% OFF
MSC Grandiosa
MSC Cruises
Dec 30, 2027 - Jan 6, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Ocean Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,210pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Nieuw Statendam
Holland America Line
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,284pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Zuiderdam
Holland America Line
Dec 5, 2026 - Dec 19, 2026 (14 Nights)
Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami
Average Starting Price
$2,034pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

47% OFF
MSC Poesia
MSC Cruises
Oct 31, 2027 - Nov 21, 2027 (21 Nights)
Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami • Kralendijk, Bonaire • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$2,060pp
Jim's Onboard Credit
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